Tonight at the Coffee Butler Amphitheater, twelve to fifteen contestants will walk onstage to unveil their headdress creations. The judges score them from the shoulders up, and the grand prize is $2,500. The Key West Business Guild presents the show, and the official schedule lists it as the Guild's 43rd Headdress Ball. Randy Roberts hosts, and WEOW's RudeGirl plays the music.
Fantasy Fest 2026, themed "Musical Icons and Iconic Musicals," started October 16 and runs through Sunday, October 25. Of the events still ahead, only one carries a crowd figure on the official listings, and that's Saturday's parade at 70,000. Most of the rest is smaller: a guild's stage show, a march the festival itself calls the Locals' Parade, decorated houses spread across the island, and a children's afternoon in Bayview Park. The festival's last stretch is held up by island organizations, with the big night in the middle.
The Four Days on One Page
| Day | Event | Where | Time | Listed cost |
|---|---|---|---|---|
| Thu., Oct. 22 | Headdress Ball | Coffee Butler Amphitheater | Doors 6:30 p.m., show 8 p.m. | Ticketed |
| Fri., Oct. 23 | Paparazzi Row, then Masquerade March | Fleming & White; lineup at Frances & Petronia | 4 p.m.; step-off 5:30 p.m. | No price listed |
| Fri.–Sat., Oct. 23–24 | Duval Street Fair | Duval Street | Noon to 2 a.m. for food | No price listed |
| Sat., Oct. 24 | Deep Eddy Vodka Fantasy Fest Parade | Old Town loop | 7 p.m. | Free |
| Sun., Oct. 25 | Children's Day | Bayview Park | Noon to 5 p.m. | No price listed |
| Sun., Oct. 25 | "The Fat Lady Sings" Tea Dance | La Te Da, 1125 Duval | 4 to 8 p.m. | $5 |
RudeGirl's name comes up all weekend. She plays the Headdress Ball tonight, calls the floats from La Te Da's street-side party on Saturday, and spins the last official dance of the festival at the same address on Sunday. The City's event notice for tonight has setup at the amphitheater starting at 8 a.m. and the show running from 8 to 11 p.m., so expect activity at Truman Waterfront Park all day.
Friday's Parade Is the One the Festival Calls the Locals'
The festival describes itself in visitor terms. Fantasy Fest Director Nadene Grossman Orr told the Key West Citizen that the festival is "a bucket-list experience, an invitation to immerse in an electrifying world of creativity, music, costumes and revelry." Friday's march gets a different label. The official schedule calls the Captain Morgan Masquerade March "The Locals' Parade," a tradition centered on "costumes, creativity and community."
The afternoon has two starting points. Paparazzi Row opens at 4 p.m. at Fleming and White Streets with a red carpet and a 360-degree selfie station. At 5 p.m. marchers line up behind the Morganettes and the band at Frances and Petronia, and the march steps off at 5:30 sharp. According to the Citizen, the route winds through Old Town and stops for drink samples at selected guest houses before it reaches the Street Fair.
Friday is also the only day the fair has arts and crafts. Craft booths run from noon to 10 p.m. and food runs until 2 a.m. Line Dancing N' the Keys, Mums the Word, The Fabulous Spectrelles and Tropicado Trio are on the entertainment lineup. On Saturday the fair is food only. Anyone hoping to buy from local makers on Duval this weekend should go Friday.
Saturday, Porches and Courtyards Become Seats
Saturday is the largest night by a wide margin. The free Deep Eddy Vodka parade steps off at 7 p.m., and the City closes Duval Street at 6. According to the City of Key West's street-closure notice, the parade starts at Truman Waterfront Park and Southard Street, turns left on Whitehead, right on Front, right on Duval, right on United, and comes back up Whitehead to the park. The City warns of traffic delays.
Along that loop, the island's porches, patios and courtyards are sold as viewing spots:
- Mangoes offers an elevated patio over Duval, $90 presale or $100 at the door, with island piano player Dave Bootle playing after the parade.
- First Flight Island Restaurant & Brewery sells sidewalk chairs starting at $125++ with a dinner buffet and open bar.
- The Smokin Tuna is back on Duval, with patio tickets starting at $300 that include dinner and a drink.
- Studio 319 puts reserved courtyard seats behind the gates of the Hellings Curry Museum, home of the Key West Woman's Club, at $350 per guest.
- The Blue Party at Kaya Island Eats in the Key West Empourium sends part of its proceeds to Sea Basecamp.
From a $90 patio to a $350 courtyard, the price is for a spot along a parade route that costs nothing to watch from the curb. On this one night, the porches and gardens of Old Town are the most valuable thing a Duval address has to offer.
Thirty-Three Façades You Can Walk
The part of the festival that reaches past Duval is the Fantasy Façades contest. Homes and businesses decorate their street-facing exteriors, and the official contest page maps all 33 entries in the Fantasy Fest app. Sloan's Haunted Key West is the contest partner. Judging took place Monday, October 19, near dark, and winners will be announced October 27.
There are eight prizes:
- Spooktacular Showstopper, best overall, $1,000
- Home Takes Center Stage, best residential take on the theme, $500
- Business Takes Center Stage, best commercial take on the theme, $250
- The Great Pumpkin, best traditional Halloween, $250
- Stagecraft, most creative design, $200
- Monster Mash, scariest display, $100
- In the Spotlight, best use of lighting, $100
- Encore, most entertaining with sound or movement, $100
The residential prize is twice the commercial one, so the contest puts more money on houses than on storefronts. It also connects to Saturday's viewing parties. KONK Life lists the Key West Woman's Club at 319 Duval Street among the 2025 winners. That's the same address selling courtyard seats for Saturday's parade. Because two of the categories reward lighting and movement, the 33 entries are probably worth seeing after sundown.
Sunday Winds Down at Bayview Park and La Te Da
The last day is quieter. Children's Day fills Bayview Park, at Truman Avenue and Eisenhower Drive, from noon to 5 p.m. with food, rides, games, arts and crafts, and a costume contest for kids. The City's notice says setup starts Saturday, so expect to see equipment in the park a day early.
From 4 to 8 p.m., "The Fat Lady Sings" Tea Dance at La Te Da closes the festival for a $5 cover, with RudeGirl on the music. On Monday, October 26, organizers announce the 2027 theme, which gives costume builders and façade decorators a year to plan. The façade winners are announced the following day.
Getting Around the Closures
The festival's parking and transportation page has the details that matter most this weekend:
- Old Town Garage, 301 Grinnell Street, has 300 first-come spaces at $6 an hour or $48 a day, subject to special-event rates. The page says residential permit holders get up to four free hours, once per day.
- Taxis and rideshares are directed to pickup and drop-off spots at or east of Simonton Street.
- Key West High School's lot takes parking Friday from 5 to 10 p.m. and Saturday from 10 a.m. to 10 p.m. A downtown shuttle runs on Saturday only, at $2 one way.
- "Resident only" street markings will be strictly enforced, and the page warns that cars may be towed.
Before Friday's march and fair, there's a quieter event on the City's calendar. Sea Dogs hosts an Early Bird Cleanup at Garrison Bight from 8 to 9 a.m. on October 23, meeting in the Garrison Bight Marina parking lot by the Dockmaster Office at 1801 North Roosevelt Boulevard.
If your Old Town porch put you in the middle of this week, or a Duval-side courtyard turned out to be the best seat on the island, it may be worth learning what that address is worth in today's market. Ocean Sotheby's International Realty knows Key West street by street, and we'd be glad to give you a clear, private picture. Request a Home Valuation, and we'll be in touch once the beads are swept up.
